Determination of the concentration of a highly reactive intermediate of saccharides utilizing the reaction kinetics of the blue bottle reaction

Iain A. Smellie, Chao Dun Tan, Iain L.J. Patterson, Georg Hähner*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

In the present study we investigated fructose, glucose, and mannose in sodium hydroxide solution. Saccharides in an alkaline solution establish a highly reactive enediolate anion of low concentration. We propose that an internal geometric rearrangement of the sugar required to establish the enediolate is responsible for different concentrations of the reactive anion depending on the sugar. We determined the free energy for the rearrangement and the concentration of the enediolate. We find that for the sugars studied there is a correlation between the magnitude of internal rotation required for hydrogen abstraction and the value of the free energy.
Original languageEnglish
Number of pages16
JournalReaction Kinetics, Mechanisms and Catalysis
VolumeOnline first
Early online date23 Jun 2025
DOIs
Publication statusE-pub ahead of print - 23 Jun 2025

Keywords

  • Saccharides
  • Reaction kinetics
  • Kinetic modelling
  • Intramolecular rearrangement
  • Enediolate concentration
  • Free energy

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